Methanesulfonyl chloride → 2,3,4,6-Tetra-O-benzyl-1,5-di-O-mesyl-D-glucitol

HRID 1025547Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1025547
[CH2:1]([O:8][C@H:9]([C@H:12]([C@@H:21]([C@@H:30]([CH2:32][O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[OH:31])[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:41](Cl)([CH3:44])(=[O:43])=[O:42]>N1C=CC=CC=1>[CH2:1]([O:8][C@H:9]([C@H:12]([C@@H:21]([C@@H:30]([CH2:32][O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[O:31][S:41]([CH3:44])(=[O:43])=[O:42])[O:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:10][O:11][S:41]([CH3:44])(=[O:43])=[O:42])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 108752501,3,4,5-Tetra-O-benzyl-D-glucitol

Produkt 1

HCID 110507692,3,4,6-Tetra-O-benzyl-1,5-di-O-mesyl-D-glucitol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel2×

Versuchsvorschrift

2,3,4,6-Tetra-O-benzyl-D-glucitol (45 g) was dissolved in pyridine (200 ml) and added over 30 min to a solution of mesyl chloride (15 ml) in pyridine (100 ml) at 0° C. The clear solution was stored at 4° C. overnight, after which time TLC analysis showed completion of the reaction. The reaction mixture was partitioned between ethyl acetate and water/ice. The organic fractions were washed with 5% hydrochloric acid then saturated aqueous sodium bicarbonate solution, dried (Na2SO4) and concentrated to a yellow/orange oil. The oil was azeotroped with toluene and used directly in the next stage.

Aufarbeitung

  1. customcompletion of the reaction
  2. customThe reaction mixture was partitioned between ethyl acetate and water/ice
  3. washThe organic fractions were washed with 5% hydrochloric acid
  4. dry with materialsaturated aqueous sodium bicarbonate solution, dried (Na2SO4)
  5. concentrationconcentrated to a yellow/orange oil
  6. customThe oil was azeotroped with toluene

Quellen und Nachweise

ORD-Eintrag
ord-7e55735e08c843f69ab6312e0a4553ea
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729099B2

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